How a Cartoon Caption Contest Can Make You a Better Writer

On the first day of my undergraduate marketing strategy course, I show my students one of my favorite New Yorker cartoons. It is an image of a familiar red-and-white-shirted man with matching cap and wooden cane. He sits at a bar. The caption states, “Nobody ever asks ‘How’s Waldo?’” It’s sharp. It mixes familiar and clever. It’s classic New Yorker humor.

While a good number of my students chuckle to themselves, few if any are regular readers of the New Yorker. Many have not even heard of the magazine, let alone its famous caption contest. But I’d like to think unfamiliarity is par for the course, as even fewer of them expect a weekly humor competition to be a graded portion of their capstone marketing class.

Each Monday of the semester, I send that week’s New Yorker caption contest to my students, who have until Friday at 5 PM to come up with their own submission. When all the entries are in, I send them to a team of friends who work in comedy full- or part-time, asking them to pick the top four. I then take those four back to the class to have the students choose their favorite. When done well, the exercise drives a lively class discussion on language and meaning, and generates a wealth of implications for future marketing professionals.

The idea first came to me when I read a post on the New Yorker blog by Cody Walker, a University of Michigan creative writing professor and New Yorker caption contest winner. Walker started his own contest a number of years ago with a group of his students at the University of Washington. As a creative writing professor, Cody’s goal is to fix the broken assumptions of the inexperienced writer. He suggests that “inexperienced writers sometimes imagine that good writing comes from good ideas. But that’s not right: good writing comes from good sentences.”

I would frame my goal a bit differently. One thing I have learned through the discipline of writing is how rarely I can assess the quality of my ideas (or lack thereof) until I write them down. For marketers, it is easy to rest in abstractions. Making general statements like “I think we can connect to Millennials with authentic branding” is a whole lot easier than writing a pitch that achieves the goal. This work of moving from general idea to powerful copy at some point requires the discipline of pen hitting the page, then revising what’s there—again, and again, and again. And I would argue the same clarity of thinking is required outside marketing too, for the entrepreneur or corporate executive designing a new strategy, for example. We need good ideas in business, and an important part of producing them is learning how to expose flaws in our thinking.

In the fall of 2014, one of our judges, Matt Sterenberg, was picked as a finalist for the real New Yorker caption contest. His entry catered to an image of two fish swimming in the sea—one as a set of bones and one in more full-bodied form. Matt’s caption read, “The relationship was less symbiotic than I’d hoped.” He ended up second in the public vote. His selection and overall finish created a lively debate among our judges and students on what worked or failed to work about Matt’s caption versus that of the public winner: “He only wanted me for my body.” Was Matt’s too obscure, too intellectual? Could he have framed his joke in a way that was more accessible? It is these kinds of discussions that help us better understand and work through the power and flexibility of language.

This playfulness with words is at the core of combining disparate thoughts, of standing ideas on their head, and it has a great deal to do with the right-brain/left-brain integration required in a business vocation. In my experience, business students and leaders too often rely on a style of thinking that seems cut-and-pasted from some first-year MBA case or bland management theory, or that’s generated creatively but without a corresponding rigor of thought. To the extent that we think in words, cultivating the discipline of writing is one practice toward clear and creative thinking. This is true whether we work in writing or business, live in for-profit or nonprofit worlds, make our home on Wall Street or Main Street.

While asking a busy business executive to flesh out a creative long-form article or book chapter is a bit unrealistic, a weekly discipline of submitting for a caption contest is a move in the same direction. Returning every week to the journey from an image to an idea to a punchy joke is a great way to train playful and disciplined thinking, and it has value whether done individually, within a classroom, or across a larger organization. In this way, I find the caption contest to be a helpful pedagogy in the most unlikely of places. And if, in the end, what results is merely a future of business with a splash of New Yorker humor, then I would venture we still all come out ahead.